All Upcoming events

• Sat, 03 Jan, 2026 - 09:00 AM

  All Kinds of Minds : A Build-Your-Own Bullet Journal Workshop

  23140 Moakley St. Suite 6, Leonardtown, MD, United States, Maryland 20650

  12+ Interested
• Sat, 28 Mar, 2026 - 09:00 AM

  Easter Extravaganza

  Town Market LLC 22675 Washington Street, The Bell Bldg Unit 106, Leonardown MD

  97+ Interested
• Fri, 26 Dec, 2025 - 08:00 PM

  All Sinners Night @ The Rex w/Smoke Signals & DJ PAPERS (Free Show)

  The Rex

  216+ Interested
• Sun, 26 Apr, 2026 - 08:00 AM

  Spring Fling Open Market & Car Show

  22675 Washington Street, The Bell Bldg, Leonardtown MD

  28+ Interested
• Sat, 27 Dec, 2025 - 06:00 PM

  Sound bath Journey

  22660 Washington St

  USD 27
• Fri, 13 Feb, 2026 - 08:30 PM

  Silent book club-SOMD Feb 2026

  Antoinette's Garden

  19+ Interested
• Sat, 27 Dec, 2025 - 07:00 PM

  Luck of the Draw

  25470 Point Lookout Rd, Leonardtown, MD 20650

  11+ Interested
• Sat, 31 Jan, 2026 - 08:00 PM

  Foreign Company at The Rex, Leonardtown MD

  The Rex

  83+ Interested
• Sat, 27 Dec, 2025 - 09:00 PM

  🎉 RΞΦ Party House Presents: The Rex House Rager 🎉

  22695 Washington St, Leonardtown, MD, United States, Maryland 20650

  25+ Interested
• Thu, 08 Jan, 2026 - 06:00 PM

  First BEACON Coalition Meeting

  41680 Miss Bessie Dr., Ste 201, Leonardtown, MD, United States, Maryland 20650

  14+ Interested
• Thu, 12 Feb, 2026 - 06:00 PM

  Galentine's Sip & Shop Happy Hour

  22695 Washington St, Leonardtown, MD, United States, Maryland 20650

  148+ Interested
• Wed, 31 Dec, 2025 - 08:00 PM

  Socials Obsidian Masquerade

  41655 Fenwick St, Leonardtown, MD

  82+ Interested
• Wed, 07 Jan, 2026 - 06:00 PM

  Trivia Night @ The Rex!

  22695 Washington St, Leonardtown, MD

  7+ Interested
• Wed, 07 Jan, 2026 - 05:30 PM

  Nicotine Cessation Class - Standalone Sessions

  21580 Peabody St, Leonardtown, MD, United States, Maryland 20650
• Sat, 24 Jan, 2026 - 08:00 PM

  DMATF@The Rex Leonardtown

  The Rex

  158+ Interested
• Fri, 16 Jan, 2026 - 06:15 PM

  Sip & Paint night Jan 2026

  23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

  38+ Interested
• Wed, 14 Jan, 2026 - 05:30 PM

  January Meet & Greet

  Leonardtown Library

  22+ Interested
• Sat, 17 Jan, 2026 - 08:00 PM

  THE BASSMENT – A 7SOUNDSCAPE TAKEOVER

  The Rex Theatre
• Fri, 16 Jan, 2026 - 06:15 PM

  Paint and Sip

  Port of Leonardtown Winery

  18+ Interested
• Wed, 07 Jan, 2026 - 12:00 PM

  Welcome Back Wednesdays (weekly workshops) - January 2026

  22660 Washington St, Leonardtown, MD, United States, Maryland 20650

  4+ Interested
• Sun, 28 Dec, 2025 - 04:00 PM

  💥Little Mania Midget Wrestling LIVE at The Rex Theater! 💥

  22695 Washington St, Leonardtown, MD, United States, Maryland 20650

  37+ Interested
• Wed, 07 Jan, 2026 - 07:30 PM

  Begin Where You Are: A Yoga Workshop

  23140 Moakley St. Suite 6, Leonardtown, MD, United States, Maryland 20650
• Wed, 31 Dec, 2025 - 09:00 PM

  Champagne Kisses & Midnight Wishes: New Years Eve Party

  22695 Washington St, Leonardtown, MD

  64+ Interested
• Sat, 27 Dec, 2025 - 02:00 PM

  Bob Pinnola and Rosa Hance at Port of Leonardtown Winery on December 27th, 2pm-5pm

  Port of Leonardtown Winery

  6+ Interested
• Thu, 22 Jan, 2026 - 07:00 PM

  🚨 WAKA FLOCKA FLAME LIVE at The Rex Theater! 🚨

  22695 Washington St, Leonardtown, MD, United States, Maryland 20650

  9+ Interested
• Fri, 02 Jan, 2026 - 10:00 AM

  The Old Jail Museum Open for Leonardtown First Fridays (Extended Hours)

  41625 Courthouse Dr, Leonardtown, MD, United States, Maryland 20650
• Sun, 18 Jan, 2026 - 01:00 PM

  Beginner Plus Two Chunky Yarn Hand Kit Workshop

  Refined Beauty: Permanent Makeup & Lash Artistry

  8+ Interested
• Wed, 31 Dec, 2025 - 12:00 PM

  Strut into the new year party!!

  40845 Merchants Lane Unit 100, Leonardtown, MD, United States, Maryland 20650

  21+ Interested
• Sat, 14 Feb, 2026 - 09:30 AM

  Valentines' Day Sweets & Treats

  Town Market LLC

  41+ Interested
• Thu, 29 Jan, 2026 - 09:00 AM

  Adult and Pediatric First Aid/CPR/AED Course

  21580 Peabody St, Leonardtown, MD, United States, Maryland 20650
• Mon, 26 Jan, 2026 - 05:00 PM

  2026 Scholarship Fair

  Dr. James A. Forrest Career And Technology Center

  20+ Interested
• Sat, 12 Sep, 2026 - 11:00 AM

  Vendors of Southern MD

  Town Market LLC

  14+ Interested
• Tue, 28 Apr, 2026 - 11:00 AM

  State of the Schools

  Dr. James A. Forrest Career And Technology Center

  13+ Interested
• Sat, 09 May, 2026 - 09:30 AM

  Mom's Day Out

  Town Market LLC

  13+ Interested
• Sat, 14 Mar, 2026 - 09:00 AM

  Stab & Gab - March 2026

  Leonardtown Library

  8+ Interested
• Sat, 17 Jan, 2026 - 09:00 AM

  Stab & Gab - Jan 2026

  Leonardtown Library

  14+ Interested
• Fri, 27 Nov, 2026 - 10:00 AM

  Holiday Market with The Grinch & Cindy Lou Who

  Town Market LLC

  10+ Interested
• Sat, 24 Jan, 2026 - 06:00 PM

  Break the Winter Blues with Mixed Tape (a Straight Vibin' Production)

  Breton Bay Golf & Country Club

  4+ Interested
• Sat, 03 Jan, 2026 - 08:00 PM

  Open Mic Night | Actions Lounge & Billiards

  25470 Point Lookout Rd, Leonardtown, MD 20650-3828, United States
• Fri, 02 Jan, 2026 - 04:00 PM

  Meet & Greet at The Good Earth (meet new owner Abby & a farewell to current owner Valerie!)

  41675 Park Ave, Leonardtown, MD, United States, Maryland 20650

  108+ Interested
• Sat, 24 Jan, 2026 - 06:00 PM

  Escape to the Tropics Party 🌴🐠

  21935 Society Hill Rd, Leonardtown, MD

  16+ Interested